


Pretty Boy

by Sorryimnotthatkindofdoctor



Category: Supernatural
Genre: Blow Jobs, Dean is a dirty-mouthed son of a bitch, M/M, Multi, NSFW, Rimming, Threesome, Voyeurism, Wincest - Freeform, cum-play, gagging, male reader - Freeform, threesome with male reader
Language: English
Status: Completed
Published: 2016-05-29
Updated: 2016-05-29
Packaged: 2018-07-10 21:45:16
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 2,782
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7009297
Author URL: https://archiveofourown.org/users/Sorryimnotthatkindofdoctor/pseuds/Sorryimnotthatkindofdoctor
Summary: <blockquote class="userstuff">
              <p>The male reader gets picked up at a bar by Sam & finds out that he has just struck the jackpot with a pair of brothers.</p>
            </blockquote>





	Pretty Boy

**Author's Note:**

> Teaser:
> 
> “Who’s this pretty young thing that’s been keeping you away from me, Sammy?” he asked, voice dark and sinful. You tensed slightly, a moment of fear at a jealous boyfriend zinging through you before it was replaced with a jolt of pleasure as Sam rolled his hips into you and chuckled.
> 
> “You were playing pool,” Sam said, turning his head away to let the other man nip at his neck. “I got bored.”
> 
> “I didn’t know Sam was taken,” you said, pulling your hands away, looking to make an escape if necessary.
> 
> “Take it easy, pretty boy,” the other man said, easily grabbing your shirt and holding you to the wall. “Sam can play with who he likes… as long as he’s willing to share.” You shuddered at the thought of being between the two of them, your cock pressing painfully against your zipper.
> 
> “This is m’brother,” Sam slurred as the other man’s free arm circled around his chest so that they were plastered close together. “Dean.”
> 
> “Your brother?” you asked, voice dropping. Dean’s green eyes zeroed in on you, predatory and protective.
> 
> “You got a problem with that?” he asked. You shook your head and then hesitated before offering a shit-eating grin.
> 
> “No, no problem… except I may have just cum in my jeans.”

Sam shoved himself into your space, a broad thigh between your legs. The pounding classic rock from the jukebox set a rhythm for you both to follow. The bar was full, but you didn’t care – the corner was dark, your dick was hard, and Sam’s thigh was providing just the right amount of pressure to make you curl your fingers into his hair and groan, your eyes closed in pleasure.

Suddenly, a second set of hands was on you, & Sam was shoved forward into you. Your eyes snapped open as you felt yourself smothered between Sam’s broad chest and the wall. Another man, not as tall as Sam but still tall enough to tower into your space, was pressed up against Sam’s back.

“Who’s this pretty young thing that’s been keeping you away from me, Sammy?” he asked, voice dark and sinful. You tensed slightly, a moment of fear at a jealous boyfriend zinging through you before it was replaced with a jolt of pleasure as Sam rolled his hips into you and chuckled.

“You were playing pool,” Sam said, turning his head away to let the other man nip at his neck. “I got bored.”

“I didn’t know Sam was taken,” you said, pulling your hands away, looking to make an escape if necessary.

“Take it easy, pretty boy,” the other man said, easily grabbing your shirt and holding you to the wall. “Sam can play with who he likes… as long as he’s willing to share.” You shuddered at the thought of being between the two of them, your cock pressing painfully against your zipper.

 “This is m’brother,” Sam slurred as the other man’s free arm circled around his chest so that they were plastered close together. “Dean.”

 “Your brother?” you asked, voice dropping. Dean’s green eyes zeroed in on you, predatory and protective.

 “You got a problem with that?” he asked. You shook your head and then hesitated before offering a shit-eating grin.

 “No, no problem… except I may have just cum in my jeans.” Dean answered your grin, tightening his grip in your shirt. With a yank, both you and Sam were pushed out the back exit, Dean steering the two of you to the parking lot. You made the ride to a motel wedged in the front seat of a cherry ride, Sam and Dean’s thighs firm and strong against yours. Dean drove with one hand on the wheel and one hand rubbing at your inseam. Sam sucked at your neck, his teeth leaving a line of pretty bruises across the flesh.

 “When we get inside,” Dean said quietly, like your spine wasn’t about to liquefy and spill out in your jeans, “I wanna watch my baby brother open you up. Wanna watch you fuck yourself on his tongue.”

“Fuck me,” you groaned, panting as Sam palmed the bulge under your zipper.

 “Sounds like a plan to me,” he whispered.

It took almost no time to get out of the car and into the motel room, Dean moving like a man on a mission. Once inside, you found yourself held between them, the brothers working in tandem to strip you of your clothes, hands and teeth exploring your flesh as it was exposed. Sam knelt in front of you to help you kick off your shoes and pull off your socks as Dean worked the button and zipper of your jeans open, shoving the denim down your hips.

“C’mon Sammy,” Dean said, wrapping an arm around your waist and hooking his head over your shoulder to look down at his brother. “Let’s see that pretty cock of his.” You shuttered in Dean’s grip, glad of his arm to help hold you up as Sam grabbed at the belt loops and pulled. You stepped out of them, feeling Sam hook his fingers in the elastic of your black boxers. He slowly pulled them down your thighs until the waistband was just below your balls. The material pressed your cock up, the flushed head swollen and shiny with precum.

Sam leaned forward, licking a long stripe up your cock, tongue tracing the vein that ran from your balls to just under the head.

“Fuck, Sam,” you said, hands going to into Sam’s hair. He groaned as he let you pull him onto your cock, lips wide and thin around the length of it. Dean let you stroke yourself in and out of Sam’s wet heat for a few moments before he pulled you away from him.

“Don’t you worry, pretty boy,” he said in your ear, voice dark and full of promise. Sam stood & moved to the bed, pulling off his shirt and popping the buttons on his jeans as he sat on the corner of the mattress. You’d felt the bulk of him pressed against you in the bar, but the sight of the bulge under his hand… You shivered.

“Stretch him good, Sammy.” Dean turned you around and forced you back until you felt Sam’s hands on  your hips. He tugged your boxers down to your ankles and you stepped out of them. He pushed at you until your legs were spread wide around his knees and you were bent slightly forward at the waist, hands on your own knees for balance.

You felt Sam’s hands firm on your ass, spreading your cheeks wide. A groan punched out of your gut as Sam set to work. He didn’t tease you – his tongue lapped at your hole a few times before the tip of it began to slowly push at your rim. Sam worked you open with his tongue, slipping the first joint of his thumb inside every now and then. It felt like hours, your thighs quivering with a combination of exertion and pleasure.

Once again, you were jolted back to the present as Dean’s hands found their way onto your body. One hand gripped into your hair, forcing your head back. His other hand wrapped around your jaw, thumb tracing along the sharp edge of your cheekbone.

 “You and Sam were having a pretty good time at the bar,” he said. “And I know just how good Sammy is with that tongue of his.” You jolted as Sam slid two spit-slick fingers inside, scissoring them to spread you wide to get his tongue even deeper inside you. Dean chuckled. “I’m feeling a little left out.”

 “Can’t – ah, fuck!” your back arched as Sam’s fingers found your prostate. “Can’t have that,” you finished when you could breathe again. Dean echoed the dirty grin on your face.

 “Open your mouth, pretty boy,” he said, thumb playing at your lip. You sucked at his thumb, tongue pressing it against the roof of your mouth as your teeth closed gently on the main joint. Dean worked his thumb in and out for a few seconds before pulling it away completely, one-handedly opening his jeans and shoving them & his jockey shorts down just low enough to get at his cock.

You braced your hands at his hips, lips opening wide to suck in his length. Dean sank in slowly, only stopping when you gagged slightly as his cock bumped the back of your throat. He pulled back and let you slide off. A thin line of saliva and precum hung from the head of his cock and your lips. You let your tongue slip out and swipe it away.

“It’s ok,” you gasped as Sam now steadily worked 3 fingers into you alongside his tongue. “Do it. You can do it.” Dean pulled you back on his cock, hands a vice grip on your head as he set up a strong rhythm in and out of your mouth. Each stroke tempted your gag reflex. Your eyes watered and spit dripped down your chin.

 “So good, Sammy,” Dean said, listening to you gag. “He’s so good.” You felt Sam pull away, leaving his fingers inside you.

 “Just wait,” he said, a wet smacking sound coming as he wiped at his chin with the back of his hand. “He’s tight, De. So fucking tight. I think I could stretch him for days and he’d still be tight.”

You groaned as the brothers talked about you while they used your body for their pleasure. Sam went back to tasting you and Dean continued to stroke in and out of your mouth, occasionally forcing the head down your throat to feel you groan around him.

 “Want to come all over that pretty face,” Dean groaned, his hips stuttering and starting to lose some of his finesse. You pulled off him completely, licking your lips. Dean took over, his fingers wrapped around his swollen length, pumping hard and fast. His thumb swiped across the slit on the upstroke, gathering precum to smooth the stroke, even though it was already soaked with your spit.

 “Only if your brother licks it off,” you said, your grin turning into a grimace of pleasure as Sam’s thick fingers worked into you again and again.

 “Fuck, yes,” Dean groaned, then, “Sammy…” Dean manhandled you, pulling you up and pushing you to the side so that you could sit on the bed near Sam. Dean crowded in close, kicking your knees apart to get even closer, his fist a blur on his cock. You watched as Dean chased his release, forearm muscles tight and veined. Dean threw his head back, biting his bottom lip and then letting his tongue swipe at the teeth marks. Sam worked a hand up your back, tangling his fingers in the hair at the back of your neck. He yanked, forcing your head back. You willingly opened your mouth, wanting to catch some of Dean’s taste on your tongue.

Dean came on a string of profanity, long stripes of cum landing on your cheek,  your jaw; one felt along your exposed neck. Dean kept stroking, eventually slowing down as a last few drops fell pearly-white across your chest.

 “Cum-covered pretty boy,” Dean breathed, face flushed with the last pleasure of his release.

 “Looks tasty,” Sam said. You looked over at him from the corner of your eye, head still pulled back. His lips were swollen and his chin spit-slick and shiny. He leaned down and slowly began to lap up the white lines of his brother’s cum from your heated flesh. Sam lay back, pulling you over to straddle his hips as he continued to lick you clean. You felt Dean reach over to your chest, scooping his cum onto his already covered fingers.

 “Dean…” you groaned as you felt him slowly start to push his cum into your hole. He slid 3 sticky fingers inside you, stretching you wide, stopping every few seconds to gather more cum from your chest before Sam could lick it all up.

 “Trust me, pretty boy,” he said, pushing another bit inside. “See, Sammy’s hung like a horse. You’ll swear you can feel it against the back of your teeth when he slides in deep.” Your hips hitched as he hit your prostate. “You’re gonna need all the slick you can get.”

 “What I need,” you moaned, dick hard and heavy between your legs, “is someone to fuck me.”

 “Looks like that’s my job,” Sam said, pulling one of your hands down to cover the bulge between his thighs.

 “On your hands and knees, pretty boy,” Dean ordered. You gasped as he pulled his fingers out of you, but moved to obey. You crawled off Sam and set yourself on all fours crosswise on the bed. Sam stood and took his clothes off while Dean pulled a bottle of lube from his duffle & tossed it on the bed.

Sam knelt behind you on the bed, acres of skin covering you like a blanket as he pressed against you, lips leaving a wet line across your shoulders. You felt his cock sliding between your cheeks, thick and heavy. You groaned as he pulled away. There was the snick of him opening the lube, then the soft squelch as he stroked a layer on his cock.

You watched as Dean pulled a chair up in front of you, sitting near the bed. He’d kicked off his boots and taken off his shirt, but still wore his jeans, pulled up but unbuttoned. His cock was limp and pale against the dark denim.

 “You ready?” Sam asked, one hand at your hip, thumb rubbing circles over the bone. You felt the slick tip of his cock at your rim.

 “Fuck yes,” you breathed and then your back bowed as Sam slowly started to push inside  you. Dean was right – Sam was huge. Even after all Sam and Dean’s prep, even though he was moving slow, even though it felt like Sam had covered himself in half a bottle of lube, you could still feel the burn as his cock split you open. You felt Dean’s cum oozing out around the push of Sam’s body into yours, the warmth of it running down your spread thighs.

Once he was slotted fully inside you, cock filling every inch your body could offer him, Sam settled against you. His length pressed hard against your prostate, a constant burn of pleasure racing through your body.

 “Sam – ah… fuck, Sam… please…”

Sam began to move then, massive hands wrapped around your shoulders to give him added leverage. Not that he needed it. His hips snapped forward and you bit your lip so hard it split, the coppery taste of blood on your tongue. Dean leaned forward and rubbed at it with his thumb.

 “Feels good, right pretty boy?” You nodded. The room suddenly didn’t seem to have enough air as Sam pounded into you. Sam sat back on his knees, using his grip on your shoulders to pull you up with him so that you sat back on his lap. His cock impossibly slid deeper inside you.

 “Oh…” was all you could say, eyes rolling up as Sam shifted his grip to your hips and began to bounce you on his length. You could tell you’d have dark bruises across your hip bones later from the strength of Sam’s grip. Dean sat back, rubbing at his cock as he watched Sam fuck you. Your own cock was hard enough to hammer nails, the constant brush of Sam against your prostate making it weep. It left shiny, slick trails of precum across your belly as you bounced.

 “You gonna cum for us, pretty boy?” Dean asked, leaning forward.

 “Yeah, yeah,” you chanted. “Please.” You felt one of Sam’s giant hands come around to cup your balls, holding your cock close to your body as he fucked you.

 “Let’s see it, pretty boy,” Dean said with a filthy grin. “Cum for me.” Your body seized tight around Sam and your vision whited out at the edges as you finally came, pulse after pulse of heat streaking from your cock and landing on your chest, dribbling down Sam’s fingers.

 “Fuck!” Sam hollered in your ear as he felt you squeeze him. He slammed you down and you felt him release inside you, hot spurts painting your insides. It made your dick jump in his hands, another jolt of cum shooting from you to cover his knuckles. Sam came forever – you could feel it leaking out around his softening cock, tracing the lines Dean’s cum had made earlier down  your thighs.

Sam wrapped his free hand around your waist and held you tight against him as the aftershocks of pleasure ran through you both, your head laying back on his shoulder. You felt the bed shift and opened your eyes to see Dean kneeling before you. He grinned before leaning down to slowly lick your cum off your belly and chest, gathering it all up before raising back up and leaning in close.

Sam hooked his head over your shoulder and met Dean halfway. The older man opened his mouth wide, your cum covering his tongue as he slowly pushed it past his little brother’s lips. You groaned, listening to the wet sounds of Sam sucking on his brother’s tongue near your ear.

 “That was hot, pretty boy,” Dean said when he pulled away. You felt him press his body closer to you, felt the hard line of his erection against the sensitive flesh of your own spent cock.

 “You ready to go again, De?” Sam asked, breathless, but still a firm block of muscle behind you. Dean nodded.

 “Want to watch you fuck him,” Sam said and you shuddered. “Fuck him until he’s hard again, and then I want you to keep fucking him while he’s inside me.” Dean rested his forehead against yours.

 “That sounds like a plan, eh pretty boy?”

 

END


End file.
